US2910377A - Heat-sensitive copying-paper - Google Patents

Heat-sensitive copying-paper Download PDF

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Publication number
US2910377A
US2910377A US594540A US59454056A US2910377A US 2910377 A US2910377 A US 2910377A US 594540 A US594540 A US 594540A US 59454056 A US59454056 A US 59454056A US 2910377 A US2910377 A US 2910377A
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Prior art keywords
heat
paper
sensitive
copying
silver
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US594540A
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English (en)
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Owen Richard
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3M Co
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Minnesota Mining and Manufacturing Co
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Priority to NL218538D priority Critical patent/NL218538A/xx
Priority to BE558766D priority patent/BE558766A/xx
Priority to NL106780D priority patent/NL106780C/xx
Priority to US594540A priority patent/US2910377A/en
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to DEM34572A priority patent/DE1193971B/de
Priority to CH4775757A priority patent/CH364800A/de
Priority to DEM58359A priority patent/DE1232991B/de
Priority to GB20589/57A priority patent/GB866076A/en
Priority to FR1200724D priority patent/FR1200724A/fr
Priority to US84855059 priority patent/US3028255A/en
Application granted granted Critical
Publication of US2910377A publication Critical patent/US2910377A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498—Photothermographic systems, e.g. dry silver
    • G03C1/4989—Photothermographic systems, e.g. dry silver characterised by a thermal imaging step, with or without exposure to light, e.g. with a thermal head, using a laser
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/165—Thermal imaging composition
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic
    • Y10T428/31884—Regenerated or modified cellulose
    • Y10T428/31888—Addition polymer of hydrocarbon[s] only

Definitions

  • Figure 1 schematically illustrates in cross-section one method of copying a graphic original
  • FIG. 2 similarly illustrates an alternative method
  • Figure 3 illustrates in cross-section a preferred form of heat-sensitive copying-paper.
  • thermo-copying machine widely employed for copying oflice records on heat-sensitive copying-paper includes as the source of radiant energy a high-intensity infrared lamp such as a GE T-3 lamp having a linear coiled filament supported within a reflector which focuses the radiation in a narrow beam across the sheet as the latter is moved past the lamp assembly.
  • a high-intensity infrared lamp such as a GE T-3 lamp having a linear coiled filament supported within a reflector which focuses the radiation in a narrow beam across the sheet as the latter is moved past the lamp assembly.
  • a lamp draws 1350 watts at 280 volts to provide a color temperature of about 2800 K.
  • Irradiation and copying of a conventional letter-size sheet requires about 16 seconds.
  • a non-fading copy is directly produced by such irradiation and without any subsequent processing such as developing, fixing, washing, treatment with fumes or vapors, or any other treatment.
  • the copying-sheet 11 of Figure 1 consists of a heatsensitive layer 15 on a carrier 16, which may be a thin paper.
  • the sheet must transmit sufiicient of the radiant energy to provide the required release of heat at the printed areas 13 but is preferably sufiiciently visibly opaque to provide high contrast in the copy.
  • Still greater accuracy of copy is obtained by inverting against a metal test bar heated to about -120" C the copying-paper 11 so that the heat-sensitive layer 15 is more closely associated with theprinted surface of the graphic original 12.
  • a visibly transparent carrier 16 permits viewing of the copy areas 14 through the carrier and in the same direction as the original.
  • the front-printing process of Figure 1 is applicable to a Wide variety of originals and to radiation-transmissi've copy-paper, whereas back-printing is most effective with originals printed on relatively thinheattransmissive paper and the copy-paper may be fully opaque to the radiation employed.
  • Figure 3 illustrates a further variation in heat-sensitive copying-papers in which the heat-sensitive layer 35 is applied to a carrier web 36 and is covered with a protective layer 37.
  • Either or both of web 36 and layer 37 may be visibly transparent, but in a preferred con-. struction for front-printing operations the web 36 is transparent while the thin protective layer 37 is visibly opaque and provides high visual contrast for the visibly changed areas of the. heat-sensitive layer.
  • Heat-sensitive copying papers suitable for the copying of printed and other graphic originals by methods just described have previously been developed, and such products are described in Miller et al. Patents Nos. 2,663,6542,663,657, in Taylor et al Patent No. 2,668,126, and in Clark et a1. Patent No. 2,710,263.
  • the sheet materials of the present invention operate through a different mechanism than do these prior art materials and provide a number of advantages thereover, as will be pointed out hereinafter in connection with illustrative but non-limiting examples.
  • those of the present invention are suitable for making direct, high contrast, clear detail, permanent copies of typewritten, printed, and other graphic subject-matter.
  • the copypaper does not adhere to nor deface the graphic original or the thermoprinting apparatus. It is stable at normal room and storage temperatures, and in particular may be stored in the light without visible change either before or after heat-copying.
  • the present invention additionally provides for the utilization of new classes of visibly heatsensitive compositions, and in a preferred modification makes available a white sheet which converts to a dense black at the heatedimage areas, thus closely duplicating the appearance of the usual typewritten or printed original.
  • the heat-sensitive coating an intimate mixture of components including an oxidizing agent and a reducing agent which when sufiiciently heated, as in the thermocopying process described, undergo an oxidationreduction type reaction resulting inthe formation of one or more visibly distinct reaction products.
  • these components are normally employed in conjunction with a water-resistant film-forming binder, the combination being in the form of either a self-supporting thin film or a thin coating on a suitable paper or other carrier web.
  • the reactants are present in amounts sufficient to provide adequate visible change on heating, and the binder maintains the reactants in the required intimate association and in position on the paper backing.
  • Additional components, both inert and chemically reactive may be included to improve the appearance or handling properties of the sheet, or to provide a more intense or differently colored heat-image, or for other purposes.
  • Example 1 A mixture of equal mol percent of silver behenate and behenic acid is prepared by reacting together one mol of silver nitrate and two mols of sodium behenate, made from commercial behenic acid, in aqueous medium and in the presence of nitric acid. The resulting waterinsoluble precipitate is recovered on a filter and iswashed and dried to produce a fine powder. The powder fuses at about 135 C. and melts to a liquid at about 175 C. Silver behenate and behenic acid, prepared separately from the same sodium behenate, melt at about 220 C. and about 70 C. respectively.
  • protocatechuic acid (3,4-dihydroxybenzoic acid, melting at about 199 C.), is separately dissolved, together with 8 parts of polystyrene resin and 2 parts of diphenyl phthalate, in 38.5 parts of ethyl acetate.
  • the two mixtures as above prepared are mixed together, producing a coating composition containing 9.5% non-volatile materials.
  • This composition is coated on 25 lb. map overlay tracing paper, a thin, non-porous, lightly calendered and substantially transparent carrier web, at a thickness sufficient to provide approximately one-half gram of the non-volatile components per square foot of coated area. This corresponds to about 25 milligrams of silver metal per square foot of area.
  • the coated sheet After drying, the coated sheet is in condition for use.
  • the sheet is stable on prolonged storage and on exposure to light, and has excellent handling properties.
  • the two mixtures may alternatively be separately applied to the paper base, with intermediate drying.
  • the reactants are intimately associated at the interface, and the sheet produces visible but somewhat less distinct copy when tested as a heat-sensitive copying-paper.
  • Example 2 The copying-paper of Example 1 is further coated, over the heat-sensitive coating, with a thin layer of a mixture of 3 parts by weight of styrene-isobutylene copolymer (Parapol S-50 resin), 66 parts of hexane, 30 parts of zinc oxide and one part silica gel (Santocel C), the mixture being ball milled for 8-26 hours to provide a viewed from the uncoated side, i.e., through the transparent paper.
  • styrene-isobutylene copolymer Parapol S-50 resin
  • 66 parts of hexane 66 parts of hexane
  • zinc oxide zinc oxide
  • silica gel Surlica gel
  • Omitting the opacifying pigments from the coating composition provides a clear transparent protective layer which prevents surface marring and otherwise protects the heat-sensitive layer while permitting it to be seen through the coating.
  • Such a structure is of particular value where an opaque or colored paper or other backing member is desired.
  • Example 3 A suspension of 6 parts by weight of the silver behenate: behenic acid mixture of Example 1 is dispersed in a solution of 1.5 parts of polystyrene resin in a mixture of 16 parts heptane and 26.5 parts acetone by ball milling to a smooth dispersion. Separately, 1.5 parts of methyl gallate, 0.1 part of 2,3-dihydroxybenzoic acid, and 0.2 part of phthalic anhydride are stirred into a solution of 11.6 parts of polystyrene resin in 13.6 parts heptane and 23 parts acetone. The two solutions are blended together and the blend coated smoothly on map overlay tracing paper, the dried coating weighing 0.5 gram per square foot, equivalent to about 21 milligrams of silver.
  • inhibitors e.g., citric acid
  • phthalic anhydride e.g., citric acid
  • the sheet is then further coated with 0.5-1.5 grams per square foot dry weight, of a smooth dispersion of 30 parts of zinc oxide, 3 parts of Parapol S-SO resin, 1 part of Santocel C filler, and 0.08 part of phthalic anhydride in 66 parts of heptane.
  • the product is white in appearance. It does not discolor on prolonged storage at normal room and storage temperatures, nor on exposure to sunlight. When pressed against a printed page and the latter intensely irradiated as hereinbefore described, the sheet darkens to a lustrous black appearance at the heated areas and provides a clear, sharp duplicate of the original printed matter.
  • Example 4 Approximately equimolar amounts of silver acid phthalate and a mixture of isomeric forms of 4-methoxy, 1- hydroxy-dihydronaphthalene available from Universal Oil Products Co. as UOPl524l22B Antioxidant) are combined with polystyrene resin binder in solution in a mixture of heptane and acetone, and the composition is coated on paper and dried, as described in'connection with Example 3. A sheet is produced which, when exposed to a heat-pattern as already described, yields a greenish image at moderate exposure and a brownish image under increased exposure. The stability of the sheet is improved by incorporation of small amounts of phthalic acid.
  • Example 5 Mercuric behenate is combined with methyl gallate by procedures as already described to provide an initially colorless stable coating which produces a brownish green image when employed as a heat-sensitive coppying-paper as herein described.
  • the metal ion is reduced to a lower valence state without visible change, whereas the methyl gallate is oxidized to a visibly diflerent compound providing the visible image.
  • Example 6 Ferric stearate is employed as the oxidizing agent and the 4rgethoxy, 1-hydmXy-dihydronaphthalene mixture of. Example 4 as the reducing agent.
  • the resulting stable heat-sensitive copy-paper yields a blue image on a butt background.
  • Example 7 Gold stearate and 2,5-dihydroxybenzoic acid produce a very pale purple stable heat-sensitive copy-paper which is converted to a purplish black image in the thermo copying process. The initial slight color is believed to be due to impurities in the gold stearate. The image areas are at least in part composed of metallic gold.
  • Example 8 A mixture of cerium stearate and the 4-methoxy, lhydroxy-dihydronaphthalene reducing agent of Example 4 provides a colorless stable heat-sensitive copy-paper yielding a. blue image.
  • Example 10 Tetradecyl amine molybdate and hydroquinone are mixed with resinous binder solution and coated on a carrier web, all as hereinbefore described, to provide an uncolored stable heat-sensitive copy-paper which produces red-brown image areas,
  • Example 11 Mercuric behenate is employed as an oxidizing agent and hydroquinone as a reducing agent.
  • an oxidationresistant mixture of tris(p-diethylaminophenyl) methane and a slight excess of dodecyl amine In order to provide for a more intense image than is obtained with these components alone, there are also included an oxidationresistant mixture of tris(p-diethylaminophenyl) methane and a slight excess of dodecyl amine.
  • the faintly greenish heat-sensitive copy-paper made with such composition when subjected to the copy-process as herein described, initially is only slightly changed in appearance. After standing in the air for a few minutes, or at most for a few hours, a dark blue image develops at the heated areas.
  • Silver behenate employed in Examples 1 and 3, is a preferred example of an organic acid salt of a reducible metal which, as has been shown by analysis of the resulting image areas, is reduced to the free metal during the oxidation-reduction reaction.
  • the silver content is readily reduced to metallic silver.
  • the compound is colorless, visibly stable toward light, insoluble in many volatile liquid vehicles, and moisture-resistant. It is produced in the desired physical form without difficulty and at reasonable cost.
  • Silver stearate has been successfully substituted for silver behenate, and silver salts of many other organic acids have also been found useful in these heat-sensitive compositions and copying-papers.
  • a partial list of such organic acids includes oleic, lauric, hydroxystearic, acetic, phthalic, terephthalic, butyric, m-nitrobenzoic, salicylic, phenylacetic, pyromellitic, p-phenylbenzoic, undecylenic, camphoric, furoic, acetamidobenzoic and o-aminobenzoic.
  • Protocathechuic acid when used in conjunction with the silver behenate: behenic acid combination of Example 1, provides a system which is initially free of color, is stable at normal room and storage conditions, reacts rapidly at temperatures well within the range of the apparatus and method employed, and produces a lustrous black image area having maximum contrast against the white background of the copying-paper.
  • Methyl gallate alone is not quite as effective, but the addition of suitable modifiers as in Example 3 produces an eminently satisfactory stable heat-sensitive copyingpaper.
  • Copying-paper made with propyl gallate and silver behenate reacts effectively at temperatures in the neighborhood of l00 C.
  • the combination of the silverreducing agent with the dispersion of organic silver salt produces a visibly heat-sensitive coating which when briefly heated well above its normal stable storage temperature reacts to liberate free silver and to produce a visible change.
  • Reducing agents which have been found useful in providing such combinations include the following; pyrogallol; 4-azeloyl-bis-pyrogallol; 4-stearoyl pyrogallol; galloacetophenone; di-tertiary-butyl pyrogallol; gallic acid anilide; methyl gallate; ethyl gallate; normaland iso-propyl gallate; butyl gallate; dodecyl gallate; gallic acid; ammonium gallate; ethyl protocatechuate; cetyl protocatechuate; 2,5 -dihydroxy benzoic acid; l-hydroxy-Z- naphthoic acid; Z-hydroxy, 3-naphthoic acid; phloroglucinol; cathechol; 2,3-naphthalene diol; 4-lauroyl catechol; sodium gallate; protocathechualdehyde; 4- methyl esculetin; 3,4-dihydroxy benzoic acid;
  • Combinations of silver salt, reducing agent and binder in the absence of the free organic acid as used in Example 1 have provided useful heat-sensitive coatings which in the form of heat-sensitive copying-papers were sufiiciently stable and produced adequate visible change for many non-critical applications. Stability towards exposure to light is improved by selecting highly purified materials; freedom from halides and sulfides is particularly important in the case of compositions involving silver salts. Stability towards both light and moisture is improved by the inclusion of free organic acid as provided in the formulas of Examples 1 and 3. Behenic acid and similar water-insoluble organic acids are particularly effective.
  • the proportions of free acid and silver salt may vary widely and the free acid may be omitted entirely; but equimolar proportions as shown in Example 1 are preferred and best results are ordinarily obtained within the approximate acid: salt molar ratios of 1:3 to 3:1. 1
  • An amount of silver salt sufficient to represent at least about 20 milligrams of silver metal per square foot of sensitive layer is found to produce fully adequate image density in the sheet material of Example 1.
  • the amount of reducing agent in such sheet accordingly should likewise be at least sufficient to reduce a quantity of silver ion equivalent to about 20 milligrams of silver per square foot of sensitive layer. Since some reagents, particularly some of the organic reducing agents, may be volatilized to some slight extent during prolonged storage prior to use, such components may be added in greater than stoichiometrically equivalent proportions; but equivalent proportions are normally preferred. Less effective but still visibly distinct image areas may be produced at still lower concentrations.
  • ammonium stearate to a gallic acid: silver'behenate combination results in a sheet which darkens slowly on prolonged storage but with which images of a variety of colors have been obtained, the color varying with the temperature and with the rate of heating employed.
  • Stability of the heat-sensitive composition is influenced adversely by the presence of water. It is therefore desirable to employ resinous binders which are substantially non-absorptive of moisture and olfer maximum protection to the reactive components. Polystyrene resins are particularly effective. Less moisture-resistant binders r 8 a may frequently be improved by the incorporation of small amounts of waxes or other moisture-proofing materials. Moisture-resistant surface coatings are also helpful;
  • the map overlay tracing paper has been replaced by other fibrous and non-fibrous sheet materials such as Monarco paper and cellophane, and the coatings are found to be operable also when applied to wood, leather, fabrics, and many other substrates, or as selfsupporting films.
  • Ethyl cellulose is useful as a filmforming binder material although somewhat less moisture-resistant than polystyrene resin. Where plasticizers for the resinous binder are found to be desirable, phosphates and phthalates, having low water absorption properties, are superior to glycols and their esters.
  • Zinc sulfide, titanium dioxide, diatomaceous earth, and numerous other pigments and fillers are useful in conjunction with the protective surface coating; metal powders and carbon black, for example, may be used in substantial proportions in back-printing copying-papers, and have been found useful in very small proportions in the surface coatings of front-printing papers, e.g., to provide somewhat higher sheet temperatures. Pigments and other particulate materials such as glass cullet or sphericles may also be added to the heat-sensitive coating for special purposes where desired.
  • Silver behenate, and silver stearate to a somewhat lesser extent, is substantially insoluble in ethyl acetate and in heptane-aectone mixtures at normal room temperatures and is mixed with the other components of the heatsensitive coating in the form of a dispersion or suspension in such solvents or mixtures, as indicated in Examples 1 and 2.
  • Most salts having a relatively high degree of solubility in a particular vehicle have been found to react with the reducing agent to an extent sufiicient to cause undesirable darkening of the liquid mixture and of the dried coating. In such cases it is ordinarily possible to select for the vehicle a volatile liquid in which either the oxidizing agent, or the reducing agent, or both are substantially completely insoluble.
  • the components may be dissolved together in a mutual solvent held at reduced temperature, and then coated and dried without heating, to provide useful heat-sensitive copying-paper.
  • a heat-sensitive copying-paper for making clear and sharp copies of graphic subject matter by methods involving brief application of a heat-pattern corresponding to said graphic subject-matter as herein described, said copying-paper being visibly stable at normal room and storage temperatures and under exposure to light, said copying-paper including a visibly heat-sensitive layer containing, in intimate association, one mol of silver behenate, about one mol of behenic acid, and and about one-half mol of protocatechuic acid.
  • a heat-sensitive copying-paper for making clear and sharp copies of graphic originals by methods involving brief application of a heat-pattern corresponding to said graphic original as herein described, said copyingpaper being visibly stable at normal room and storage temperatures and under exposure to'light, said copyingpaper comprising a paper base and a visibly heat-sensitive coating comprising, uniformly dispersed in intimate association in a water-resistant binder, one mol of silver behenate, about one mol of behenic acid, and about onehalf mol of protocatechuic acid.
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction of a graphic original by methods involving brief application of a heat-pattern corresponding to said graphic original as herein described, said copysheet being visibly stable under normal storage conditions and being rapidly permanently visibly changed on heating to a conversion temperature of the order of about 90-15 C., said copy-sheet including a visibly heat-sensitive layer containing, in intimate association, (1) a normally solid organic acid salt of a noble metal, and (2) a cyclic organic reducing reagent for the noble metal ions, having an active hydrogen atom attached to an atom, se lected from the class of oxygen, nitrogen and carbon atoms, directly attached to an atom of the cyclic ring, said reducing reagent being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of aqueous silver nitrate in an organic solvent, each of reagents (l) and (2) being stable against decomposition when separately heated to said conversion temperature.
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction of a graphic original by methods involving brief application of a heat-pattern corresponding to said graphic original as herein described, said copysheet being visibly stable under normal storage conditions and being rapidly permanently visibly changed on heating to a conversion temperature of the order of about 90-150 C.
  • said copy-sheet comprising a thin carrier Web and a heat-sensitive coating thereon including (1) a filmforming binder, (2) a Water-insoluble normally solid silver salt of an organic acid, and (3) an aromatic organic reducing reagent for the silver ions, having an active hydrogen atom attached to an atom, selected from the class consisting of oxygen, nitrogen and carbon atoms, directly attached to an atom of the aromatic ring, said reducing reagent being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of aqueous silver nitrate in an organic solvent, each of reagents (2) and (3) being stable against decomposition When separately heated to said
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction, in the form of black infraredabsorptive image areas on white background areas, of a black-on-white graphic original by methods as described in the accompanying specification and involving brief application of a heat-pattern corresponding to the black areas of said original, said copy-sheet being visibly stably white under normal storage conditions and being rapidly permanently converted to black on heating to a conversion temperature of the order of about 90-150" C.
  • said copysheet comprising a paper carrier web and a heat-sensitive coating thereon including (1) a film-forming binder, (2) a Waterinsoluble, normally solid, substantially colorless silver salt of an organic acid, and (3) a substantially colorless aromatic organic reducing reagent for the silver ions, having a hydroxyl group attached directly to an atom of the aromatic ring, said reducing reagent being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of aqueous silver nitrate
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction of a graphic original by methods as described in the accompanying specification and involving brief application to said copy-sheet of a heat-pattern corresponding to said graphic original, said copy-sheet being visibly stable under normal storage conditions and being rapidly permanently visibly changed on heating to a conversion temperature of the order of about 9,0-150 C.
  • said copy-sheet comprising a paper carrier Web and a heat-sensitive coating thereon including (1) a moistureresistant resinous film-forming binder, (2) a Water-insoluble normally solid organic acid silver salt, and (3) an aromatic organic reducing reagent for the silver ions, having an active hydrogen atom attached to an atom, selected from the class consisting of oxygen, nitrogen and carbon, directly attached to an atom of the aromatic ring, said aromatic reducing reagent being oxidizable with loss of aromaticity while still retaining a ring structure and being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of a
  • a heat-sensitive copy-sheet as defined in claim 4 in which the silver salt and the aromatic organic reducing reagent are present in approximately equimolar proportions.
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction of a graphic original by methods as described in the accompanying specification and involving brief application to said copy-sheet of a heat-pattern corresponding to said graphic original, said copy-sheet being visibly stable under normal storage conditions and in the presence of moisture and being rapidly permanently visibly changed on heating to a conversion temperature of the order of about 150 C.
  • said copy-sheet comprising a paper carrier web and a heat-sensitive coating thereon including (1) a moisture-resistant resinous filmforming binder, (2) a water-insoluble normally solid silver salt of a solid organic acid, (3) a quantity of a solid free organic acid, and (4) an aromatic organic reducing reagent for the silver ions, having an active hydrogen atom attached to an atom, selected from the class consisting of oxygen, nitrogen and carbon, directly attached to an atom of the aromatic ring, said reducing reagent being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of aque
  • a heat-sensitive copy-sheet for making a clear and sharp reproduction of a graphic original by methods as described in the accompanying specification and involving brief application to said copy-sheet of a heat-pattern corresponding to said graphic original, said copy-sheet be ing visibly stable under normal storage conditions and in the presence of moisture and being rapidly permanently visibly changed on heating to a conversion temperature of the order of about 90-150 C.
  • said copy-sheet comprising a paper carrier Web and a heat-sensitive coating thereon including (1) a moisture-resistant resinous filmforming binder, (2) a water-insoluble normally solid silver salt of a solid organic acid, (3) a quantity of said organic acid, and (4) an aromatic organic reducing reagent for the silver ions, having an active hydrogen atom attached to an atom, selected from the class consisting of oxygen, nitrogen and carbon, directly attached to an atom of the aromatic ring, said reducing reagent being further characterized as causing the reduction of silver ion and precipitation of metallic silver on being dissolved at moderate temperature in a solution of a

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Color Printing (AREA)
US594540A 1956-06-28 1956-06-28 Heat-sensitive copying-paper Expired - Lifetime US2910377A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
NL218538D NL218538A (en)) 1956-06-28
BE558766D BE558766A (en)) 1956-06-28
NL106780D NL106780C (en)) 1956-06-28
US594540A US2910377A (en) 1956-06-28 1956-06-28 Heat-sensitive copying-paper
DEM34572A DE1193971B (de) 1956-06-28 1957-06-27 Thermographisches Kopierpapier
CH4775757A CH364800A (de) 1956-06-28 1957-06-27 Wärmeempfindliches Kopiermaterial
DEM58359A DE1232991B (de) 1956-06-28 1957-06-27 Thermographisches Kopierpapier
GB20589/57A GB866076A (en) 1956-06-28 1957-06-28 Heat-sensitive copying paper
FR1200724D FR1200724A (fr) 1956-06-28 1957-06-28 Papier copiant thermosensible
US84855059 US3028255A (en) 1956-06-28 1959-10-26 Heat-sensitive copy-sheet

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US594540A US2910377A (en) 1956-06-28 1956-06-28 Heat-sensitive copying-paper

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Cited By (61)

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US3024362A (en) * 1958-08-09 1962-03-06 Kalle Ag Heat sensitive reproduction material and mbthod of using same
US3028254A (en) * 1959-09-21 1962-04-03 Minnesota Mining & Mfg Stabilized chemically reactive heatsensitive copy-sheet
US3028255A (en) * 1956-06-28 1962-04-03 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3031329A (en) * 1959-10-26 1962-04-24 Minnesota Mining & Mfg Heat-sensitive copy-sheet and composition therefor
US3063863A (en) * 1959-04-21 1962-11-13 Du Pont Heat-sensitive compositions and elements, and processes for using same
US3073953A (en) * 1959-07-29 1963-01-15 Du Pont Process for producing images
US3074809A (en) * 1959-10-26 1963-01-22 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3080254A (en) * 1959-10-26 1963-03-05 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3088028A (en) * 1959-02-06 1963-04-30 Columbia Ribbon & Carbon Duplication with heat-meltable solvent for hectographic coloring material
US3090697A (en) * 1961-02-13 1963-05-21 Nashua Corp Heat sensitive marking papers and methods for making same
US3094620A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Copy-sheet and method
US3094417A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Heat sensitive copy sheet, process of making and using
US3097297A (en) * 1958-07-15 1963-07-09 Heat sensitive coating
US3103881A (en) * 1958-10-20 1963-09-17 Minnesota Mining & Mfg Method of copying
US3107174A (en) * 1958-10-20 1963-10-15 Minnesota Mining & Mfg Heat sensitive copy sheet and method of making
US3108896A (en) * 1959-10-26 1963-10-29 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3109748A (en) * 1960-04-28 1963-11-05 Columbia Ribbon & Carbon Thermographic reproduction composite wherein a calcium carbonate layer is effected by a transferred heat-sensitive material
US3111423A (en) * 1960-05-16 1963-11-19 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3161770A (en) * 1962-03-20 1964-12-15 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3162763A (en) * 1962-04-05 1964-12-22 Dietzgen Co Eugene Thermographic reproduction paper, method of making and method of using
US3167651A (en) * 1962-05-15 1965-01-26 Dietzgen Co Eugene Thermographic reproduction paper and method of making and using
US3174038A (en) * 1962-06-18 1965-03-16 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3218166A (en) * 1962-11-23 1965-11-16 Minnesota Mining & Mfg Heat sensitive copy sheet
US3223526A (en) * 1959-05-28 1965-12-14 Minnesota Mining & Mfg Printing processes including size reduction of graphic intelligence
US3241997A (en) * 1961-12-23 1966-03-22 Schutzner Walter Heat-sensitive copying material
US3315598A (en) * 1960-07-28 1967-04-25 Minnesota Mining & Mfg Copying of graphic originals
US3394042A (en) * 1963-09-13 1968-07-23 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3442682A (en) * 1964-07-17 1969-05-06 Gen Co Ltd Heat-sensitive copy-sheet
US3446648A (en) * 1965-09-27 1969-05-27 Minnesota Mining & Mfg Reactive copying sheet and method of using
US3455687A (en) * 1964-11-28 1969-07-15 Eastman Kodak Co Photothermographic copying process
US3460946A (en) * 1966-02-03 1969-08-12 Minnesota Mining & Mfg Image receptor sheets containing organic silver salts and metal ion image
US3632377A (en) * 1969-01-06 1972-01-04 Minnesota Mining & Mfg Image transfer sheet and method
US3772052A (en) * 1970-09-28 1973-11-13 Fuji Photo Film Co Ltd Recording sheet and color developer therefor
US3934070A (en) * 1970-10-23 1976-01-20 Fuji Photo Film Co., Ltd. Recording sheet and color developer therefor
US4013473A (en) * 1974-08-24 1977-03-22 Agfa-Gevaert N.V. Recording materials and image receiving materials for producing copies in a dry way
US4109937A (en) * 1976-01-30 1978-08-29 Trans World Technology Laboratories, Inc. (Twt Labs Inc.) Donor sheet for thermographic imaging process
US4188212A (en) * 1976-08-18 1980-02-12 Fuji Photo Film Co., Ltd. Electric current conductive composition, image recording element containing the same and process for recording images using the same
US4379835A (en) * 1980-12-22 1983-04-12 Minnesota Mining And Manufacturing Company Black image from a thermographic imaging system
US4461496A (en) * 1982-08-17 1984-07-24 Minnesota Mining And Manufacturing Company Soap having improved carbonless imaging properties
US4604635A (en) * 1984-11-08 1986-08-05 Intermec Corporation Thermal paper and method for making thermal paper with silicone resin protective layer
US4741992A (en) * 1986-09-22 1988-05-03 Eastman Kodak Company Thermally processable element comprising an overcoat layer containing poly(silicic acid)
US5210245A (en) * 1990-12-10 1993-05-11 Mooney Chemicals, Inc. Gold carboxylates and process for preparing the same
US5275932A (en) * 1992-03-16 1994-01-04 Minnesota Mining And Manufacturing Company Thermal development accelerators for thermographic materials
EP0671283A1 (en) * 1994-03-10 1995-09-13 Agfa-Gevaert N.V. Thermal transfer imaging process
EP0713133A1 (en) * 1994-10-14 1996-05-22 Agfa-Gevaert N.V. Receiving element for use in thermal transfer printing
US5578548A (en) * 1995-10-16 1996-11-26 Minnesota Mining & Manufacturing Company Thermographic element with improved anti-stick coating
US5858913A (en) * 1994-10-14 1999-01-12 Agfa-Gevaert Receiving element for use in thermal transfer printing
US6093529A (en) * 1997-04-16 2000-07-25 Fuji Photo Film Co., Ltd. Imaging materials
US6413712B1 (en) 1999-09-17 2002-07-02 Fuji Photo Film Co., Ltd. Photothermographic material
US20030235795A1 (en) * 2001-08-22 2003-12-25 Fuji Photo Film Co., Ltd. Photothermographic material
US6682878B2 (en) 2000-12-05 2004-01-27 Fuji Photo Film Co., Ltd. Thermal development photosensitive material
US20040023174A1 (en) * 2001-03-23 2004-02-05 Tomoyuki Ohzeki Photothermographic material
WO2004043704A1 (en) 2002-11-12 2004-05-27 Sherwood Technology Limited Use of transition metal compounds in imageable coatings
EP0903628B1 (en) * 1997-09-17 2004-07-07 Agfa-Gevaert Thermographic recording material with improved stability
US20040130611A1 (en) * 2002-07-31 2004-07-08 Fuji Photo Film Co., Ltd. Shading correction method for heat development recording apparatus and heat development recording apparatus
US6764816B2 (en) 2001-03-23 2004-07-20 Fuji Photo Film Co., Ltd. Thermally developable photosensitive material
US20050231585A1 (en) * 2004-03-02 2005-10-20 Mudigonda Dhurjati S Method and system for laser imaging utilizing low power lasers
US20060062270A1 (en) * 2003-08-13 2006-03-23 Satoshi Okutani Optical device and organic EL display
US20060134567A1 (en) * 2001-09-12 2006-06-22 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and heat-developing method using the same
US7138221B2 (en) 2001-10-05 2006-11-21 Fuji Photo Film Co., Ltd. Photothermographic material
US7977040B2 (en) 2001-10-19 2011-07-12 Fujifilm Corporation Heat developable photosensitive material

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US4232083A (en) * 1975-07-22 1980-11-04 Minnesota Mining And Manufacturing Company Imaging compositions and methods
JPS61173987A (ja) * 1985-01-30 1986-08-05 Sugai Kagaku Kogyo Kk 熱転写記録体

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US2663657A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2663656A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2740896A (en) * 1947-05-10 1956-04-03 Minnesota Mining & Mfg Method of using heat sensitive copying paper
US2749253A (en) * 1952-05-20 1956-06-05 Dick Co Ab Method of making a copy sheet and resultant article

Patent Citations (4)

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US2740896A (en) * 1947-05-10 1956-04-03 Minnesota Mining & Mfg Method of using heat sensitive copying paper
US2663657A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2663656A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2749253A (en) * 1952-05-20 1956-06-05 Dick Co Ab Method of making a copy sheet and resultant article

Cited By (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028255A (en) * 1956-06-28 1962-04-03 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3097297A (en) * 1958-07-15 1963-07-09 Heat sensitive coating
US3024362A (en) * 1958-08-09 1962-03-06 Kalle Ag Heat sensitive reproduction material and mbthod of using same
US3107174A (en) * 1958-10-20 1963-10-15 Minnesota Mining & Mfg Heat sensitive copy sheet and method of making
US3103881A (en) * 1958-10-20 1963-09-17 Minnesota Mining & Mfg Method of copying
US3088028A (en) * 1959-02-06 1963-04-30 Columbia Ribbon & Carbon Duplication with heat-meltable solvent for hectographic coloring material
US3063863A (en) * 1959-04-21 1962-11-13 Du Pont Heat-sensitive compositions and elements, and processes for using same
US3223526A (en) * 1959-05-28 1965-12-14 Minnesota Mining & Mfg Printing processes including size reduction of graphic intelligence
US3073953A (en) * 1959-07-29 1963-01-15 Du Pont Process for producing images
US3028254A (en) * 1959-09-21 1962-04-03 Minnesota Mining & Mfg Stabilized chemically reactive heatsensitive copy-sheet
US3108896A (en) * 1959-10-26 1963-10-29 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3080254A (en) * 1959-10-26 1963-03-05 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3074809A (en) * 1959-10-26 1963-01-22 Minnesota Mining & Mfg Heat-sensitive copying-paper
US3031329A (en) * 1959-10-26 1962-04-24 Minnesota Mining & Mfg Heat-sensitive copy-sheet and composition therefor
US3109748A (en) * 1960-04-28 1963-11-05 Columbia Ribbon & Carbon Thermographic reproduction composite wherein a calcium carbonate layer is effected by a transferred heat-sensitive material
US3111423A (en) * 1960-05-16 1963-11-19 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3315598A (en) * 1960-07-28 1967-04-25 Minnesota Mining & Mfg Copying of graphic originals
US3094620A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Copy-sheet and method
US3094417A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Heat sensitive copy sheet, process of making and using
US3094619A (en) * 1961-01-03 1963-06-18 Minnesota Mining & Mfg Ultra-violet radiation-desensitizable thermographic copy-sheet and method
US3090697A (en) * 1961-02-13 1963-05-21 Nashua Corp Heat sensitive marking papers and methods for making same
US3241997A (en) * 1961-12-23 1966-03-22 Schutzner Walter Heat-sensitive copying material
US3161770A (en) * 1962-03-20 1964-12-15 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3162763A (en) * 1962-04-05 1964-12-22 Dietzgen Co Eugene Thermographic reproduction paper, method of making and method of using
US3167651A (en) * 1962-05-15 1965-01-26 Dietzgen Co Eugene Thermographic reproduction paper and method of making and using
US3174038A (en) * 1962-06-18 1965-03-16 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3218166A (en) * 1962-11-23 1965-11-16 Minnesota Mining & Mfg Heat sensitive copy sheet
US3394042A (en) * 1963-09-13 1968-07-23 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3442682A (en) * 1964-07-17 1969-05-06 Gen Co Ltd Heat-sensitive copy-sheet
US3455687A (en) * 1964-11-28 1969-07-15 Eastman Kodak Co Photothermographic copying process
US3446648A (en) * 1965-09-27 1969-05-27 Minnesota Mining & Mfg Reactive copying sheet and method of using
US3460946A (en) * 1966-02-03 1969-08-12 Minnesota Mining & Mfg Image receptor sheets containing organic silver salts and metal ion image
US3632377A (en) * 1969-01-06 1972-01-04 Minnesota Mining & Mfg Image transfer sheet and method
US3772052A (en) * 1970-09-28 1973-11-13 Fuji Photo Film Co Ltd Recording sheet and color developer therefor
US3934070A (en) * 1970-10-23 1976-01-20 Fuji Photo Film Co., Ltd. Recording sheet and color developer therefor
US4013473A (en) * 1974-08-24 1977-03-22 Agfa-Gevaert N.V. Recording materials and image receiving materials for producing copies in a dry way
US4109937A (en) * 1976-01-30 1978-08-29 Trans World Technology Laboratories, Inc. (Twt Labs Inc.) Donor sheet for thermographic imaging process
US4188212A (en) * 1976-08-18 1980-02-12 Fuji Photo Film Co., Ltd. Electric current conductive composition, image recording element containing the same and process for recording images using the same
US4379835A (en) * 1980-12-22 1983-04-12 Minnesota Mining And Manufacturing Company Black image from a thermographic imaging system
US4461496A (en) * 1982-08-17 1984-07-24 Minnesota Mining And Manufacturing Company Soap having improved carbonless imaging properties
US4604635A (en) * 1984-11-08 1986-08-05 Intermec Corporation Thermal paper and method for making thermal paper with silicone resin protective layer
US4741992A (en) * 1986-09-22 1988-05-03 Eastman Kodak Company Thermally processable element comprising an overcoat layer containing poly(silicic acid)
US5210245A (en) * 1990-12-10 1993-05-11 Mooney Chemicals, Inc. Gold carboxylates and process for preparing the same
US5275932A (en) * 1992-03-16 1994-01-04 Minnesota Mining And Manufacturing Company Thermal development accelerators for thermographic materials
EP0671283A1 (en) * 1994-03-10 1995-09-13 Agfa-Gevaert N.V. Thermal transfer imaging process
US5589317A (en) * 1994-03-10 1996-12-31 Agfa-Gevaert N.V. Thermal transfer imaging process
EP0713133A1 (en) * 1994-10-14 1996-05-22 Agfa-Gevaert N.V. Receiving element for use in thermal transfer printing
US5858913A (en) * 1994-10-14 1999-01-12 Agfa-Gevaert Receiving element for use in thermal transfer printing
US5578548A (en) * 1995-10-16 1996-11-26 Minnesota Mining & Manufacturing Company Thermographic element with improved anti-stick coating
US6093529A (en) * 1997-04-16 2000-07-25 Fuji Photo Film Co., Ltd. Imaging materials
EP0903628B1 (en) * 1997-09-17 2004-07-07 Agfa-Gevaert Thermographic recording material with improved stability
US6413712B1 (en) 1999-09-17 2002-07-02 Fuji Photo Film Co., Ltd. Photothermographic material
US6682878B2 (en) 2000-12-05 2004-01-27 Fuji Photo Film Co., Ltd. Thermal development photosensitive material
US20050158675A9 (en) * 2001-03-23 2005-07-21 Tomoyuki Ohzeki Photothermographic material
US20040023174A1 (en) * 2001-03-23 2004-02-05 Tomoyuki Ohzeki Photothermographic material
US7211373B2 (en) 2001-03-23 2007-05-01 Fujifilm Corporation Photothermographic material
US6764816B2 (en) 2001-03-23 2004-07-20 Fuji Photo Film Co., Ltd. Thermally developable photosensitive material
US20030235795A1 (en) * 2001-08-22 2003-12-25 Fuji Photo Film Co., Ltd. Photothermographic material
US20060134567A1 (en) * 2001-09-12 2006-06-22 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and heat-developing method using the same
US7101658B2 (en) 2001-09-12 2006-09-05 Fuji Photo Film Co., Ltd. Heat-developable photosensitive material and heat-developing method using the same
US7138221B2 (en) 2001-10-05 2006-11-21 Fuji Photo Film Co., Ltd. Photothermographic material
US7977040B2 (en) 2001-10-19 2011-07-12 Fujifilm Corporation Heat developable photosensitive material
US6914621B2 (en) 2002-07-31 2005-07-05 Fuji Photo Film Co., Ltd. Shading correction method for heat development recording apparatus and heat development recording apparatus
US20040130611A1 (en) * 2002-07-31 2004-07-08 Fuji Photo Film Co., Ltd. Shading correction method for heat development recording apparatus and heat development recording apparatus
US20060040217A1 (en) * 2002-11-12 2006-02-23 Brian Stubbs Use of transition metal compounds in imageable coatings
WO2004043704A1 (en) 2002-11-12 2004-05-27 Sherwood Technology Limited Use of transition metal compounds in imageable coatings
US7270919B2 (en) 2002-11-12 2007-09-18 Datalase Ltd. Use of transition metal compounds in imageable coatings
US20060062270A1 (en) * 2003-08-13 2006-03-23 Satoshi Okutani Optical device and organic EL display
US20050231585A1 (en) * 2004-03-02 2005-10-20 Mudigonda Dhurjati S Method and system for laser imaging utilizing low power lasers

Also Published As

Publication number Publication date
FR1200724A (fr) 1959-12-23
DE1232991B (de) 1967-01-26
BE558766A (en)) 1900-01-01
NL106780C (en)) 1900-01-01
NL218538A (en)) 1900-01-01
GB866076A (en) 1961-04-26
CH364800A (de) 1962-10-15
DE1193971B (de) 1965-06-03

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